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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1643590Generated: November 1, 2026

Triethylamine → HCID 59560293, compound

https://huagongshe.com/reaction/1643590

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant(3,5-Difluorophenyl)boronic acidHCID 2734338—
ReactantMethyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylateHCID 25067323—
CatalystCupric acetateHCID 8895—
SolventDichloromethaneHCID 6344—
ProductHCID 59560293HCID 5956029326.6%

Reaction Steps

A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxy-lic acid methyl ester (3e) (1 g, 0.0045 mol), 3,5-difluorophenylboronic acid (1.07 g, 0.0068 mol), Cu(OAc)2 (0.9 g, 0.005 mol), freshly activated 4 Å molecular sieves (4 g) and Et3N (4 mL) in CH2Cl2 (25 mL) was stirred at room temperature under N2 for 48 hrs. The mixture was filtered through Celite and the filter cake was washed with CH2Cl2. The filtrate was concentrated to give a dark liquid. The crude liquid was purified by column chromatography eluting with EtOAc/petroleum ether (1/5) to give the title compound (0.4 g, 26.6%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.18 (s, 1H), δ 7.14 (s, 1H), 6.47(m, 1H), δ 6.36 (dd, 2H), 3.81 (s, 3H), 2.83 (s, 2H), 1.41 (s, 6H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08119624B2
Source datasetuspto-grants-2012_02
ORD IDord-5f6f025061954c05aa2521eaae619775
Source noteuspto-grants-2012_02